4-(1H-benz[d]imidazol-2-yl)-2,6-di-tert-butylphenol | 3203-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(1H-benz[d]imidazol-2-yl)-2,6-di-tert-butylphenol
• 英文别名: 2-(3,5-di-tert-butyl-4-hydroxyphenyl)benzimidazole；2-(4-Hydroxy-3,5-di-tert-butylphenyl)benzimidazole；4-(1H-benzimidazol-2-yl)-2,6-di-tert-butyl-phenol；4-(1H-benzoimidazol-2-yl)-2,6-di-tert-butyl-phenol；2-<4-Hydroxy-3,5-di-tert.-butyl-phenyl>-benzimidazol；2-(3,5-Di-t-butyl-4-hydroxyphenyl)benzimidazole；4-(1H-benzimidazol-2-yl)-2,6-ditert-butylphenol
• CAS: 3203-02-9
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: JWVSBNYGKQHTQN-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  463.7±55.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1H-benz[d]imidazol-2-yl)-2,6-di-tert-butylphenol 在 lead dioxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以90%的产率得到4-(1H-benzimidazol-2-yl)-2,6-di-tert-butyl-phenoxyl radical
  参考文献：
  名称：

  Highly stabilized phenoxyl radicals with hydrogen-bonding capability

  摘要：

  The syntheses of 4-(1H-benzimidazol-2-yl)-2,6-di-tert-butyl-phenoxyl and 4-(1H-5,6-dimethylbenzimidazol-2-yl)-2,6-di-tert-butyl-phenoxyl radicals (1-2) by oxidation of the corresponding phenols is described. The radicals are stable enough to retain color for weeks in the solid state in air under some conditions. Their hydrogen bonding functionality offers prospects for use in molecular magnetic materials. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00784-4
• 作为产物：
  描述：

  2,6-二叔丁基-4-甲基苯酚 、 2-硝基苯胺 在 铁粉 、 sulfur 作用下， 以 邻二氯苯 为溶剂， 反应 24.0h， 以5%的产率得到4-(1H-benz[d]imidazol-2-yl)-2,6-di-tert-butylphenol
  参考文献：
  名称：

  Redox-Neutral Iron–Sulfur Promoted Transformation of 2-Nitrophenols and 2,6-Disubstituted p-Cresols into 2-Arylbenzoxazoles

  摘要：

  A catalyst based on iron and elemental sulfur has been shown to efficiently promote a redox-neutral reaction between 2-nitrophenols and 2,6-disubstituted p-cresols, allowing for the preparation of 2-arylbenzoxazoles in good yields. This synthetic methodology also affords high atom economy without the use of any external oxidizing and/or reducing reagents. This is the first redox-condensation reaction of 2-nitrophenols with 2,6-disubstituted p-cresols.

  DOI：

  10.1055/s-0033-1338995

文献信息

• Studies on the synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position. I.
  作者：YASUO ISOMURA、NORIKI ITO、HIROSHIGE HOMMA、TETSUSHI ABE、KAZUO KUBO

  DOI：10.1248/cpb.31.3168

  日期：——

  A number of 2, 6-di-tert-butylphenols with a heterocyclic group at the 4-position were prepared. The heterocyclic groups were as follows : benzoxazole, benzothiazole, benzimidazole, indole, imidazo [1, 2-a] pyridine and imidazo [1, 2-a] pyrimidine. Anti-inflammatory activity of these compounds was examined by using the adjuvant-induced arthritis (A. A) assay. Some compounds were further tested in carrageenin-induced rat paw edema (CIPE) assay and AcOH-induced writhing (AIW) assay in mice. The anti-inflammatory activity was greatly dependent on the value of the heterocyclic group. Among these compounds, 2-(3, 5-di-tert-butyl-4-hydroxyphenyl)-benzoxazole (IIa) and 2-(3, 5-di-tert-butyl-4-hydroxyphenyl) indole (Xg) showed very potent activity. Both IIa and Xg had a minimum effective dose of 5 mg/kg (p. o.) in A. A assay and showed stronger activity than phenylbutazone in CIPE assay but weaker analgesic activity than aminopyrine in AIW assay.

  制备了一系列在4位含有杂环基团的2,6-二叔丁基苯酚。这些杂环基团包括：苯并噁唑、苯并噻唑、苯并咪唑、吲哚、咪唑[1,2-a]喹啉和咪唑[1,2-a]嘧啶。这些化合物的抗炎活性通过佐剂诱导的关节炎（A.A）测定进行评估。部分化合物在卡拉胶诱导的大鼠足肿胀（CIPE）测定和醋酸诱导的小鼠扭动（AIW）测定中进一步测试。这些化合物的抗炎活性在很大程度上取决于杂环基团的性质。在这些化合物中，2-(3,5-二叔丁基-4-羟基苯基)苯并噁唑（IIa）和2-(3,5-二叔丁基-4-羟基苯基)吲哚（Xg）表现出非常强的活性。IIa和Xg在A.A测定中的最小有效剂量为5 mg/kg（口服），在CIPE测定中显示出比苯基布托松更强的活性，但在AIW测定中的镇痛活性则弱于氨基吡啶。
• A Bioinspired Construct That Mimics the Proton Coupled Electron Transfer between P680^•+ and the Tyr_Z-His190 Pair of Photosystem II
  作者：Gary F. Moore、Michael Hambourger、Miguel Gervaldo、Oleg G. Poluektov、Tijana Rajh、Devens Gust、Thomas A. Moore、Ana L. Moore

  DOI：10.1021/ja803015m

  日期：2008.8.13

  anisotropic coupling tensors of the phenoxyl radical are resolved in the photoinduced D-band EPR spectra and are in good agreement with previously reported g-tensors of tyrosine radicals in photosystem II. The observed temperature dependence of the charge shift is attributed to restricted nuclear motion at low temperature and is reminiscent of the observation of a trapped high-energy state in the natural system

  一种仿生混合系统，由用 PSII 叶绿素-Tyr-His 复合物的光化学活性模拟物改性的胶体 TiO2 纳米粒子表面组成，经历光诱导的逐步电子转移，并在酚类部位与质子运动耦合。低温电子顺磁共振研究表明，光激发后注入的电子位于 TiO2 纳米颗粒上。在 80 K 时，95% 的孔位于苯酚部分，5% 位于卟啉。在 4.2 K 时，52% 的孔仍被困在卟啉上。苯氧基自由基的各向异性耦合张量在光致 D 带 EPR 光谱中解析，并且与先前报道的光系统 II 中酪氨酸自由基的 g-张量非常一致。观察到的电荷转移的温度依赖性归因于低温下受限制的核运动，这让人想起在自然系统中观察到的高能态。电化学研究表明，模型系统的苯氧基/苯酚对在化学上是可逆的，并且在热力学上能够进行水氧化。
• Synthesis and antioxidant properties of benzimidazole derivatives with isobornylphenol fragments
  作者：I. A. Dvornikova、E. V. Buravlev、I. V. Fedorova、O. G. Shevchenko、I. Yu. Chukicheva、A. V. Kutchin

  DOI：10.1007/s11172-019-2510-7

  日期：2019.5

  A series of new 2-substituted-1H-benzimidazoles was synthesized on the basis of 4-hydroxybenzaldehydes. Their antioxidant properties were evaluated in the in vitro models and compared with those of known analogs. The structural specifi c features of the molecules responsible for the high antioxidant activity were revealed. Among tested derivatives, 2-substituted 1H-benzimidazole containing a phenol

  在4-羟基苯甲醛的基础上合成了一系列新的2-取代-1H-苯并咪唑。在体外模型中评估了它们的抗氧化特性，并与已知类似物的抗氧化特性进行了比较。揭示了负责高抗氧化活性的分子的结构特异性特征。在测试的衍生物中，发现含有异冰片基和叔丁基苯酚片段的 2-取代 1H-苯并咪唑在急性氧化应激条件下具有最大的保护生物分子和细胞的能力。
• Selective Oxidative Methyl C–H Functionalization of Butylated Hydroxytoluene toward Arylimines/<i>N</i>-Heterocycles
  作者：Jianyu Dong、Shaofeng Wu、Furong Geng、Yani Yan、Long Liu、Yongbo Zhou

  DOI：10.1021/acs.joc.3c01643

  日期：2023.10.20

  A metal-free and selective oxidative methyl C–H functionalization of BHT with aniline compounds has been developed. This innovative method enables the facile and efficient synthesis of a diverse array of BHT-functionalized N-containing skeletons, including arylamines, benzoxazoles, benzothiazoles, benzimidazoles, quinazolines, and quinazolinones, all of which are challenging to access. The control

  已经开发出一种无金属的苯胺化合物对 BHT 进行选择性氧化甲基 C-H 官能化的方法。这种创新方法能够轻松有效地合成多种 BHT 官能化含氮骨架，包括芳胺、苯并恶唑、苯并噻唑、苯并咪唑、喹唑啉和喹唑啉酮，所有这些都很难获得。涉及TEMP 18 O的对照实验表明TEMPO与BHT的苄基的自由基加合物可以作为中间体。
• Chemistry of 2-substituted benzimidazoles. 1. 5-Amino-2-methyl(aryl, arylalkyl, pyridyl)benzimidazoles
  作者：K. D. Ambacheu、V. G. Pleshakov、B. S. Baatkh、V. P. Zvolinskii、M. D. Kharlamova、A. A. Obynochnyi、N. S. Prostakov

  DOI：10.1007/bf02269539

  日期：2000.4